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Details

Stereochemistry RACEMIC
Molecular Formula C17H26N4O3S2
Molecular Weight 398.543
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of FURSULTIAMINE

SMILES

C\C(N(CC1=C(N)N=C(C)N=C1)C=O)=C(\CCO)SSCC2CCCO2

InChI

InChIKey=JTLXCMOFVBXEKD-FOWTUZBSSA-N
InChI=1S/C17H26N4O3S2/c1-12(16(5-6-22)26-25-10-15-4-3-7-24-15)21(11-23)9-14-8-19-13(2)20-17(14)18/h8,11,15,22H,3-7,9-10H2,1-2H3,(H2,18,19,20)/b16-12+

HIDE SMILES / InChI
Fursultiamine, also known as thiamine tetrahydrofurfuryl disulfide (TTFD) is an oral FDA- approved thiamine derivative for treating vitamin B1 deficiency and is very rapidly metabolized into thiamine. Fursultiamine possesses a mild beneficial effect in patients with Alzheimer's disease. The improvement could be observed not only in their emotional or other mental symptoms but also in intellectual function. Only mildly impaired subjects showed cognitive improvement. In addition was shown, that fursultiamine have a beneficial clinical effect on some autistic children. Some relatively recent experiments have revealed that fursultiamine was a unique antagonist of hepcidin in vitro that could serve as a template for the development of drug candidates that inhibit the hepcidin-ferroportin interaction. This inhibition is a key for the treatment of anemia of inflammation (AI), a common in patients with infection, autoimmune diseases, cancer, and chronic kidney disease.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
Palliative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Treatment of autism spectrum children with thiamine tetrahydrofurfuryl disulfide: a pilot study.
2002 Aug
Thiamine tetrahydrofurfuryl disulfide: a little known therapeutic agent.
2004 Sep
Fursultiamine, a vitamin B1 derivative, enhances chondroprotective effects of glucosamine hydrochloride and chondroitin sulfate in rabbit experimental osteoarthritis.
2005 Jun
Patents

Sample Use Guides

Single administration of 100 mg of thiamin tetrahydrofurfuryl disulfide
Route of Administration: Oral
To explore new therapeutic options for Anemia of inflammation (AI) and other iron-related disorders caused by hepcidin excess, there was developed a cell-based screen to identify hepcidin antagonists. Of the 70,000 small molecules in the library, it was identified 14 compounds that antagonized the hepcidin effect on ferroportin. One of these was fursultiamine. To fully characterize fursultiamine as a hepcidin antagonist, there was examined its dose-dependent effect on cellular iron export. Fpn-GFP cells were treated with 100 ng/ml hepcidin and 0–50 μM fursultiamine for 24 hours, and intracellular ferritin concentration was determined. Fursultiamine reversed the effect of hepcidin on ferritin levels, with the IC50 dose in the submicromolar range.
Name Type Language
FURSULTIAMINE
INN   JAN   MART.   MI   WHO-DD  
INN  
Official Name English
N-((4-AMINO-2-METHYLPYRIMIDIN-5-YL)METHYL)-N-((1E)-4-HYDROXY-1-METHYL-2-((TETRAHYDROFURAN-2-YLMETHYL)DISULFANYL)BUT-1-EN-1-YL)FORMAMIDE
Systematic Name English
ALINAMIN-F
Common Name English
ALIARON F
Brand Name English
N-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-N-(4-HYDROXY-1-METHYL-2-((TETRAHYDROFURFURYL)DITHIO)-1-BUTENYL)FORMAMIDE
Systematic Name English
fursultiamine [INN]
Common Name English
FURSULTIAMINE [MART.]
Common Name English
TTFD
Code English
FURSULTIAMIN
Common Name English
FURSULTIAMINE [MI]
Common Name English
Fursultiamine [WHO-DD]
Common Name English
FURSULTIAMINE [JAN]
Common Name English
Classification Tree Code System Code
DSLD 3907 (Number of products:11)
Created by admin on Fri Dec 15 17:10:22 GMT 2023 , Edited by admin on Fri Dec 15 17:10:22 GMT 2023
Code System Code Type Description
DRUG CENTRAL
1259
Created by admin on Fri Dec 15 17:10:22 GMT 2023 , Edited by admin on Fri Dec 15 17:10:22 GMT 2023
PRIMARY
ChEMBL
CHEMBL1740659
Created by admin on Fri Dec 15 17:10:22 GMT 2023 , Edited by admin on Fri Dec 15 17:10:22 GMT 2023
PRIMARY
PUBCHEM
3002119
Created by admin on Fri Dec 15 17:10:22 GMT 2023 , Edited by admin on Fri Dec 15 17:10:22 GMT 2023
PRIMARY
NCI_THESAURUS
C1505
Created by admin on Fri Dec 15 17:10:22 GMT 2023 , Edited by admin on Fri Dec 15 17:10:22 GMT 2023
CONCEPT Dietary Supplement
EPA CompTox
DTXSID0023084
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PRIMARY
RXCUI
4604
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PRIMARY RxNorm
EVMPD
SUB07852MIG
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PRIMARY
NCI_THESAURUS
C121852
Created by admin on Fri Dec 15 17:10:22 GMT 2023 , Edited by admin on Fri Dec 15 17:10:22 GMT 2023
PRIMARY
WIKIPEDIA
Fursultiamine
Created by admin on Fri Dec 15 17:10:22 GMT 2023 , Edited by admin on Fri Dec 15 17:10:22 GMT 2023
PRIMARY
FDA UNII
05J61265PX
Created by admin on Fri Dec 15 17:10:22 GMT 2023 , Edited by admin on Fri Dec 15 17:10:22 GMT 2023
PRIMARY
SMS_ID
100000084485
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PRIMARY
DAILYMED
05J61265PX
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PRIMARY
CAS
804-30-8
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PRIMARY
ECHA (EC/EINECS)
212-357-1
Created by admin on Fri Dec 15 17:10:22 GMT 2023 , Edited by admin on Fri Dec 15 17:10:22 GMT 2023
PRIMARY
MERCK INDEX
m5610
Created by admin on Fri Dec 15 17:10:22 GMT 2023 , Edited by admin on Fri Dec 15 17:10:22 GMT 2023
PRIMARY Merck Index
DRUG BANK
DB08966
Created by admin on Fri Dec 15 17:10:22 GMT 2023 , Edited by admin on Fri Dec 15 17:10:22 GMT 2023
PRIMARY
INN
2311
Created by admin on Fri Dec 15 17:10:22 GMT 2023 , Edited by admin on Fri Dec 15 17:10:22 GMT 2023
PRIMARY